Fiction: Underwear Swap

[this sounds awfully familiar...]


Sandra was the sweetest, most outrageously gorgeous woman I ever had the fortune to meet.  Having a relationship with her felt like winning the lottery.  I couldn't believe my luck, and I felt like I would and should do anything to keep her.  It was she who planted that dirty little seed in my head.  I still don't know if she did it on purpose.

She looked like a fashion model.  She was gorgeous even without makeup.  She always dressed revealingly, right down to her underwear, but without looking sleazy.  She always maintained a very classy, but at the same time sexy, look.  She is the type of woman who is so feminine that you wonder how she can possibly be of the same species.  She is inhumanly beautiful.

It pains me to think of her now.  I am consumed with envy at the merest thought of her.  You'll understand if I avoid going into much more detail about her.  I'll leave it to your imagination.

One time after a particularly intimate session of lovemaking, she brought up the idea that would change me in ways I never conceived of: she wanted to swap underwear.  She explained that it would make her feel closer to me if she could wear my briefs briefly.  I would have to wear her lingerie to make the exchange equal.  It would only be for a second or two, she said.  She picked up my gitch from the floor, and put it on. 

It was the funniest thing in the world to her.  They didn't fit her all that well, but she still looked pretty damned gorgeous.  Imagine that: she could even make a regular pair of gitch look feminine on her.  I don't know if it turned her on or not.  I, personally, was a bit spent from the arduous passion we had shared moments earlier.

She cajoled me into picking up her panties off the floor.  I mentioned earlier that she wore classy but sexy clothes.  Her unmentionables were no different.  Her panties were off-white silk with lacy patterns on the sides and a very dainty little bunching up at the elastics.  I won't describe how she looked in them.  They dangled from my fingers as I looked at them stupidly.  I tried to reconcile what seemed to me two impossibly disparate concepts.  Sandra's panties.  My crotch.  North Pole and South Pole.  Two positive ends of a magnet.  The two could not possibly come in contact together, unless I was dry humping her as she wore them.  For me to wear them seemed not only absurd, but physically impossible.  She giggled behind me.  Clearly, this was quite amusing to her.  I wasn't even sure whether I was amused or not, the idea perplexed me so much.

"What are you afraid of?" she chided, "You think wearing them will make you less of a man?"

She hit the nail on the head.  A classic dilemma: do I do what the most absolutely perfect woman in the world, whom I am most impossibly fortunate to have as a girlfriend, wants me to do, even if it undermines my masculinity?  If I refuse, I risk losing her for not playing along; if I accept, I risk losing her for not being manly enough.  Which would you choose?  Pray that this never happens to you.  In fact, my telling you this now will probably ruin you just as it did me.  Don't say I didn't warn you.  Maybe you should stop reading right now, if you know what's good for you.

In the end, it didn't matter.  I had lost the moment she expressed that thought.  I had been presented with a possibility that did not exist in my conception of the universe.  My world became unraveled at that moment, even though I struggled mightily to keep it together.  There I stood, naked, the threads of my world bunched together in a ball of lint in one hand, Sandra's intricate, beautiful, but durable panties in the other.

Days afterwards, I could think of nothing else.  So it goes when your perceptions become fundamentally altered by a new idea.  I still could not understand all of the consequences of the idea of wearing Sandra's panties.  I needed time to think about it.  It drove me to distraction.  Would wearing the epitome of femininity's most intimately feminine clothes damage my manhood?  If so, then doesn't that prove my manhood to be incredibly weak?  I saw her wearing my underwear, and she maintained her womanhood.  If anything, she made my gitch feminine.  But then again, I am not nearly as masculine as she is feminine.  Plus, manhood is much more fragile, ironically, than womanhood.  Women never worry if they're feminine enough.  Men struggle daily to prove their sexuality.  Men can never prove enough.  If a woman were caught wearing men's underwear, no one would question her sexuality.  She would remain a woman no matter what.  But if a man wears women's underwear, he brands himself a sissy at the very least.  His manhood becomes forever suspect.  But then, what kind of man would refuse to test his manhood?  Doesn't it show fear, a most unmanly thing, to refuse to wear women's underwear?  Sandra herself joked about it to me.  Am I so underconfident that I wouldn't dare to wear something designed for women?  Isn't my manhood strong enough.

These thoughts consumed me for weeks.  Imagine thinking about the most gorgeous woman in the world and her underwear constantly.  It's like being a pubescent teen again.  Inevitably, I would work myself into a passionate frenzy thinking about Sandra's panties.  Never mind the consequences, what would it be like to wear them?  And what about other garments?  What about bras, bathing suits, miniskirts, stockings, garter belts?  What would it be like to wear makeup?  Heels?  Shave my legs?  Every time I thought about it, I imagined what it would feel like to actually wear these things.  I imagined how Sandra looked in all of them, and how they felt from the outside, and tried to picture how it would feel from the inside.  It drove me crazy.  It drove me to relieving my tension.  It aroused more than curiosity to think of it.

I became more and more interested in what she wore.  She never brought up panty swapping again, but I was captivated by her lingerie all the more.  I couldn't dare bring it up myself.

I began to worry about my obsession with her clothes.  I thought about wearing her underwear.  Ever since the idea was introduced to me, I could suddenly conceive of the possibility of such a thing.  I imagined every possible consequence, even the absurd.  It could have absolutely no effect.  Or it could instantly change my sex, and transform me into a woman as beautiful as Sandra. I knew that neither was true, and that reality was somewhere in between.  I must admit that I dwelt far more on the latter scenario, and that such thoughts eventually brought unparalleled satisfaction.  In plain English: I became aware that the thought of wearing Sandra's panties turned me on.  In a big way.

At first I denied it.  It couldn't possibly be true.  But there I was, masturbating every time I imagined myself in her panties, or her bikini, or her nightgown, or whatever, and metamorphosing into a woman.  The shame I felt afterwards was unbearable.  I figured that as long as I didn't actually do it, I would be in no danger of losing my masculinity.  The very thought of losing my masculinity actually turned me on even more.  It was only a matter of time.

When I finally found myself alone with Sandra's panties, I shook with dread.  Part of me absolutely had to wear those panties.  Part of me resisted.  The latter part lost.  I dared to put them on for a few seconds, took them off immediately, and ran off to masturbate.  As long as I didn't do it with them on, I would surely be fine, I thought, while deep down I knew that I had contaminated myself with femininity, and hoped that it would only get much, much worse.  I promised myself that I wouldn't ever have to wear anything like it again, because now I knew what it's like.  I also promised myself that I would wear nothing but women's clothes from then on and officially become a woman right then and there.

Of course, I moped with shame after I was done.  I had succumbed most brutally to femininity.  I swore to never do it again.  The very next day, Sandra's laundry still wasn't done, and I still had her panties at my apartment.  I wore them longer than the last time, with the exact same result.  How I wanted to wear them longer!  How I wanted to wear all her clothes, and experience the full gamut of women's clothing!  How I kicked myself after I was done and cursed that my manhood would now slowly erode, and swore to never even think about it again.

I tried to fool myself that I was protecting myself by keeping on my male socks as I masturbated in them.  How I tricked myself into believing that I could get away with wearing them under my clothes all day long.  None of it mattered, as I eventually succumbed to dressing fully as a woman, and reveled in my girlishness, knowing that I was doomed to becoming more and more effeminate the further I went, and loving every second of it.